Methanol → 121679-21-8

HRID 358592Notes

Reaction equation

HRID 358592 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[OH-:17].[K+].[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1.[CH3:27][OH:28]>>[C:23]([OH:26])(=[O:4])[C:27]([OH:28])=[O:17].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH:22]=1)(=[O:5])=[O:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 134757652-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

Product 1

HCID 20066733121679-21-8

Procedure

A solution of N-methyl-1H-indole-5-ethanesulphonamide (1.0 g) in methanol (50 ml) containing potassium hydroxide (5.6 g) and N-methyl-4-piperidone (1.0 ml) was heated at reflux for 24h, cooled, and the resulting solid filtered off (1.0 g). A sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g), the solution cooled, and the salt precipitated by adding ethyl acetate (20 ml) and dry ether (50 ml). The salt was filtered off, and dried in vacuo to give the title compound as a solid (0.12 g) m.p. 87°-90° (shrinks) Analysis Found: C,52.2; H,5.6; N,9.5. C17H23N3O2S.C2H2O4.0.6H2O requires C,52.5; H,6.0; N,9.7%.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationthe resulting solid filtered off (1.0 g)
  4. dissolutionA sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g)
  5. temperaturethe solution cooled
  6. customthe salt precipitated
  7. additionby adding ethyl acetate (20 ml) and dry ether (50 ml)
  8. filtrationThe salt was filtered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-36c743241eb8401dbd961db09df5d8c6
Source dataset
uspto-grants-1991_03
Patent number
US04997841

Reaction notes

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